Reaction of organotin hydrides with acid chlorides. Mechanism of aldehyde and ester formation

…, E Lusztyk, B Maillard, KU Ingold

Index: Lusztyk, J.; Lusztyk, E.; Maillard, B.; Ingold K. U. Journal of the American Chemical Society, 1984 , vol. 106, # 10 p. 2923 - 2931

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Citation Number: 19

Abstract

Abstract: Tri-n-butyltin hydride reacts with acid chloride, RCOCI, spontaneously at ambient temperatures to form n-Bu3SnC1, RCHO, RC (0) OCH2R, and a number of minor products. The reaction is not a radical chain process, nor are radicals involved as intermediates. The initial products are n-Bu, SnCI and RCHO; it is not known whether these are formed in a direct reaction between n-Bu3SnH and RCOCl or via an unstable chloroalkoxytin species, ...